For the third year in a row, we escaped this past weekend for a heavy dose of holiday memories to a city that pours out festive feels from every corner, every storefront window, every street musician.
My kids look forward to our Christmas weekend in Chicago as much as Christmas itself, but this year perhaps no one was excited about this trip as much as Lainey. Her best friend Maggie moved to a Chicago suburb over the summer, and while the loss of her presence here has been patched over with FaceTime calls and daily texts, technology has nothing on the hug they shared an hour after we arrived and the three days that followed that included these two joined at the hip.
Christmas in Chicago musts for us include:
State Street Macy’s window displays.
Numerous stops for hot chocolate while we sightsee.
Riding the train.
Pictures on my friend’s apartment stoop.
…and so many night walks where we point out Christmas trees in windows and look for parties and pick which front door decorations are our favorites. We imagine the stories that are written in all the buildings we walk past, and my dad provides an ongoing soundtrack with the portable speaker he keeps in his pocket, full volume–all the Christmas carols, all the time.
New favorites this year:
Tea at the Drake Hotel with our friends and Brett’s sister (who is moving to Naples in just days, and we are so excited!).
A night time carriage ride through the city (we used Antique Coach & Carriage Co., just outside the old Water Tower). We all loved this one so much and will definitely do it again.
You bundle up beneath blankets and ride through the most festive streets, even a little stretch along Lake Shore Drive. We sang Christmas carols while the kids hollered to onlookers various holiday greetings that, I’m sorry to say, included “Tooty Christmas!”, “Happy Toots!” and “We Wish You a Merry Fart!” (followed by hysterical laughter).
Macy’s Santa. We’ve never attempted Santa in Chicago before because the lines were too long (because it’s the REAL Santa) and Nella isn’t much for seeing him face-to-face, but I was on a one-on-one date with Nella and ventured down to the enchanting Santa Land in Macy’s where Santa was visiting. I thought maybe we’d just check it out, but we came during a time when there were no lines, so I pushed it a little further, standing in line and suggesting we’d just “look at Santa.” not sit with him. When it was our turn, the red velvet curtain pulled back to reveal this magical festive nook and the kindest Santa, straight from the North Pole. When Nella was hesitant, sweet Santa suggested I sit with her alone while he walked away. Once she was comfortable, we asked if he could come back and she said yes. I asked if I could step away to take a picture, and she nodded yes again. And then Santa reached for a book and asked if he could read it to her. I didn’t think to check my camera settings–just started snapping. Magic, I tell you.
I don’t know how I missed the little playground tucked right next to the fire station near Michigan Ave all these years, but I’m so glad we found it this year. It was warm enough that the kids could actually enjoy a good half hour playing there before our next cocoa stop.
Another favorite this year was Christkindlmarket, an open-air German holiday village full of gift vendors and German food. I enjoyed my first (and hopefully not last) cup of Glühwein, the most delicious hot spiced wine, and picked up some keepsake treasures.
At the Bean, it was surprisingly warm enough for the kids to take off their coats for a bit.
Even though we didn’t end up with snow, we feel so lucky to have enjoyed such beautiful weather when we’ve experienced brutal winds on this weekend before. The sun allowed for more outdoor exploring.
And when the sun went to bed and the cold came creeping in, we made my favorite memories–the indoor kind, not dependent on what the city gave to us but what we brought to it.
Our wonder…
…our dance moves…
…and the suitcase of things we packed to “make it special.” Snowmen marshmallows for cocoa, a Christmas puzzle, our favorite jammies, card games and a candle that smells like a Christmas tree farm.
My dear friend lets us stay at her family’s apartment, and so many of our most memorable moments on this weekend happen inside this special place, set up with toys and so many little personal touches.
I think we could have skipped the city adventures altogether and let Nella play in this secret nook the whole weekend, and she would have been perfectly happy.
We’re smitten with this city and so grateful to tuck away another weekend of December memories together here.
…and even happier to come home to be together as a family, where we belong.
xo to you and yours.
Kelly gavIn says
Awesome! I might do it instead of nyc next year! Any hotel recommendations? (PME mom)
Kelle says
I’ve stayed at several different hotels there, but I love the Allegro. Some of the older hotels are great too–full of character. Also, I always buy my tickets September/early October and get the same deal–Spirit Airlines, from Fort Myers to Ohare, around $112 round trip. So affordable!
Kim says
How old are you kids? The Swissotel has a Santa Suite you can visit and get hot chocolate and decorate cookies. The Gwen has fun things for older kids like rooftop Curling. So many great places to stay in Chicago at Christmastime!
Anne says
We’ve stayed at the Blackstone. Love it.
pamela says
Wow that is an awesome deal with the airfare, thank you very much for sharing & the timeframe. Love that you’re making this a tradition each year – so special & magical.
jessey says
I love reading about all your traditions, and as a fellow lover of Christmas and especially Christmas in the city, I looked forward to your re-cap and as always, your words and pictures are fantastic…..
Now to await your other cold-weather trip- Jackson Hole is a place we love so dearly that me and the husband are going for a repeat trip next year, without the kids (!) but hope to get there in winter as a family someday.
Kelly says
The Santa story with Nella made me cry. So beautiful. What an amazing Santa.
Natalie C says
I used to live in Chicago and I have to say this brings back all the good stuff! I’ve done all you mentioned! Next year you should see The Nutcracker! It is AMAZING! I’ve been to several in many cities and Chicago’s is the best! Plus you can get the pretty women balcony seats for less than 50 bucks!
Sara piller says
We were at Christkindlmarket this weekend too. It was PACKED when we were there. We could barely walk! Looks like it was a bit less crowded for you! It’s one of our new traditions with our kids (this was our second year). My kids love it!
Anne says
One year when you are here with good weather you must visit Maggie Daley Park! It’s close to the Bean and the BEST playground ever!!
Jennifer Reil says
You are so magical! I love the sweet photos of your kiddos and that your dad carries Christmas carols in his pocket. I’ve got to get a portable speaker now :).
Lindsay Kearns says
Magical weekend in a magical city! Can you share where you got both your adorable Christmas PJs and the snowmen marshmallows!
Kelle says
PJs are Hanna Andersson, marshmallows are Williams Sanoma
Andrea says
All heart eyes for the girls’ heart sweaters! Where are they from?
Kelle says
Forever 21 girls
Mr. Ed’s teeth/ heeee-hawwww says
Aww..come on Kelle….you still simmerin’ on that Rwanda post? Still waiting for it! Lololol…
Kelle says
I don’t usually approve silly comments like this, but this one’s a fun one to publish because I am truly flattered that, in a quickly changing Internet world deeply saturated with so many blogs to read, you’re still showing up here. Rwanda was how many years ago–I think five? And you still make time to pop over here and look at pictures. It’s nice to know that something draws you back, even if it’s my teeth and hair!
Rosemary Sullivan says
Beautiful post as always. You can get the mulled wine at Trader Joe’s and Aldi’s. Pour in a mug and microwave. My 33 year old daughter turned me on to it. Merry Christmas
MV says
Thanks for sharing! My little family is headed there this weekend!
Kristi says
Kelle,
Do you think sometime you could write a post about your thoughts on blending a family?
Thanks!
Kristi
Mandi Wolfswinkel says
Hey Kelle!
Christmastime in Chicago seems magical! We are taking our kids to Chicago in February for a “Christmas” trip. We tend to do that instead of a lot of gifts. We are planning to take them to Medieval Times and the boys are headed to the car show, but I wondered if you/other locals or experienced people might have some ideas for me that we could do with our kids (15, 11, and 8) in February that isn’t the norm on a list of places. I’d love to get creative. Let me know if you have any ideas!! I would be truly grateful.
dmwolfswinkel@hotmail.com
Stephanie says
We visit Chicago often, and one of our favorite indoor family spots is The Game Room at the Chicago Athletic Association Hotel, right on Michigan Ave across from the Bean. It’s a bar, but full of foosball and shuffleboard tables, and with great snacks and drinks to keep everyone warm and happy. Ice-skating on the ribbon at Maggie Daley Park is wonderful, too! You can rent skates right there (though the line can be long). Enjoy!
Bonnie says
Even though I live in Chicago, I look forward to seeing it through the eyes of you and the children. Oh, and I think it is such a hoot that your day totes his own Christmas music. I hope I run into you some day. Merry Christmas!
Best,
Bonnie
LAURA ORTIZ says
Love all your posts and like many, I also wait for this one, the Chicago post. I love how you describe your weekend there and all the fun things you make your kids experience.
Your dad reminds me of mine, he passed a few years ago, he was always making sure we were having fun.
suzan says
OH how precious. Little people and festive moods seem to be enhanced by the colder weather. I live in a hot and humid part of Australia and it always strikes me as cruel that we sing cold weather carols.
Enjoy your Christmas.
Jenni says
The pic of Nella with Santa just melted my heart, Merry Xmas xx
Debbie From illinois says
Chicago is such a fun city. Thanks for sharing. Merry Christmas!??
Jean Shea says
This is such an amazing way to create new memories with your children! All the photos are pure magic, not just the Santa one. I love it all!